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  1. $3,946 to $9,975/night

    Casa Royale- Luxurious Waterfront Living

    6 BedroomsBathroomsSleeps 14
    1 night minstay
    Pool
    FREE CANCELLATION
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  3. $3,502 to $8,050/night

    Beach Castle

    7 BedroomsBathroomsSleeps 18
    3 nights minstay
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  5. $2,733 to $10,688/night

    Wailea Beach Villa B102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  7. $2,662 to $8,312/night

    Domus Pacis | 2590 E County Highway 30A

    7 BedroomsBathroomsSleeps 20
    3 nights minstay
    Pool
    FREE CANCELLATION
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  9. $2,653 to $9,501/night

    Wailea Beach Villa B202

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  11. $2,423 to $9,090/night

    Andaz Villa 810

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $2,072 to $8,559/night

    3902 Pacific Zen

    6 Bedrooms7.5 BathroomsSleeps 14
    2 nights minstay
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  15. $1,836 to $5,138/night

    Curious Tides- 3132/3134 Estero Blvd- 20% off April + Ma...

    10 BedroomsBathroomsSleeps 24
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  17. $1,662 to $5,684/night

    Halama Hale Private Home

    4 Bedrooms3.5 BathroomsSleeps 14
    2 nights minstay
    Pool
    FREE CANCELLATION
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  19. $1,604 to $2,164/night

    Moloa'a Bay Villa & Cottage

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $1,604 to $2,164/night

    Moloa'a Bay Villa & Cottage

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
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  23. $1,515 to $8,454/night

    40 Goshawk

    5 Bedrooms5.5 BathroomsSleeps 12
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
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  25. $1,495 to $4,313/night

    Dream On

    4 Bedrooms4.5 BathroomsSleeps 14
    2 nights minstay
    Pool
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  27. $1,420 to $2,846/night

    Park Place | 89 Watercolor Blvd

    5 Bedrooms5.5 BathroomsSleeps 14
    3 nights minstay
    Pool
    FREE CANCELLATION
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  29. $1,420 to $3,135/night

    Summer Villa | 274 Pompano Street

    7 Bedrooms8.5 BathroomsSleeps 18
    3 nights minstay
    Pool
    FREE CANCELLATION
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  31. $1,306 to $2,007/night

    Inviting Vacation Home Directly on Beach

    7 Bedrooms5.5 BathroomsSleeps 14
    2 nights minstay
    Pool
    FREE CANCELLATION
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  33. $1,249 to $1,605/night

    Swami's Sunset *New Listing*

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
    Pool Hot Tub
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  35. $1,240 to $3,226/night

    229 Faraway The Ridge #35

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
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  37. $1,183 to $3,402/night

    Sea Dream | 1960 E Co Hwy 30A

    4 Bedrooms4.5 BathroomsSleeps 12
    3 nights minstay
    Pool
    FREE CANCELLATION
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  39. $1,183 to $2,426/night

    Minnow Mansion | 2804 E Co Hwy 30A

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
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  41. $1,141 to $4,247/night

    The Cove Hale

    4 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  43. $1,101 to $4,619/night

    Wailea Beach Villa M312

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  45. $1,098 to $3,736/night

    Big Island Hale Kaheka 6592

    1 Bedroom2.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  47. $1,091 to $4,200/night

    Wailea Elua 1603

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  49. $1,083 to $1,459/night

    Luxury Makalae Home close to Water Activities

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $1,083 to $1,459/night

    Makalae

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $1,065 to $4,762/night

    Enchantment | 305 Pompano Street

    5 BedroomsBathroomsSleeps 16
    3 nights minstay
    Pool
    FREE CANCELLATION
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  55. $1,063 to $1,861/night

    66 Thackwell Lane

    4 Bedrooms3.5 BathroomsSleeps 8
    3 nights minstay
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $1,020 to $3,078/night

    Sunset Tides- 3134 Estero Blvd 20% Off April + May!

    5 Bedrooms4.5 BathroomsSleeps 12
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  59. $1,020 to $2,260/night

    Coastal Tides- 3132 Estero Blvd- 20% off April + May!

    5 Bedrooms4.5 BathroomsSleeps 12
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  61. $1,017 to $2,101/night

    Baydream

    4 Bedrooms3.5 BathroomsSleeps 23
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  63. $1,014 to $4,254/night

    Big Island Hualalai 133C

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  65. $1,010 to $5,255/night

    803 Holden Rd.

    5 Bedrooms5.5 BathroomsSleeps 14
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
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  67. $1,006 to $3,059/night

    Shellstone Cottage | 8690 E Co Hwy 30A

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
    Pool
    FREE CANCELLATION
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  69. $1,005 to $6,801/night

    7 Bedroom Private Pool Spa Home Walking distance to Beac...

    7 Bedrooms7.5 BathroomsSleeps 17
    2 nights minstay
    Pool Pets OK
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $998 to $1,275/night

    Kahana Outrigger #1A2

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  73. $990 to $3,435/night

    Forever Sunshine- Beach Vacation Rental

    9 BedroomsBathroomsSleeps 26
    1 night minstay
    Pool Pets OK
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $989 to $8,081/night

    The Timber Lodge 957

    7 BedroomsBathroomsSleeps 19
    2 nights minstay
    Hot Tub
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $987 to $4,721/night

    Wailea Beach Villa I503

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $987 to $2,858/night

    Big Island Aloha Pearl House

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $985 to $3,394/night

    Robason Residence

    6 BedroomsBathroomsSleeps 16
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $980 to $4,934/night

    Ho'olei 17-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $969 to $1,772/night

    Majestic Beach House with Private Pool and Fishing Dock ...

    7 Bedrooms6.5 BathroomsSleeps 17
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $960 to $4,334/night

    349 Holden Rd.

    5 BedroomsBathroomsSleeps 14
    2 nights minstay
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $960 to $4,672/night

    Highlands Slopeside #221

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $952 to $2,383/night

    3772 The Waves

    3 Bedrooms3.5 BathroomsSleeps 5
    1 night minstay
    Pets OK
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $945 to $6,233/night

    75 Palms

    8 Bedrooms7.5 BathroomsSleeps 23
    2 nights minstay
    Pool Hot Tub Pets OK
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $936 to $1,411/night

    Sands Of Kahana 384

    1 BedroomBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $936 to $2,545/night

    Mauna Pua- A 7 bedroom Kauai Vacation Rental

    7 BedroomsBathroomsSleeps 14
    3 nights minstay
    Hot Tub
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $935 to $4,001/night

    Ho'olei 112-5

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $935 to $3,582/night

    Wailea Beach Villa H202

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $932 to $5,665/night

    PLANTATION HOUSE on Palma Sola Bay Private Pool And Boat...

    7 BedroomsBathroomsSleeps 19
    2 nights minstay
    Pool Hot Tub
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $927 to $2,784/night

    Summit Cabin at Lakota

    4 Bedrooms4.5 BathroomsSleeps 10
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $909 to $3,743/night

    Lupine Residence

    5 Bedrooms5.5 BathroomsSleeps 14
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $897 to $5,404/night

    Northridge Mesa

    7 Bedrooms4.5 BathroomsSleeps 14
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $896 to $1,456/night

    HOKUEA HALE

    3 Bedrooms2.5 BathroomsSleeps 10
    3 nights minstay
    Hot Tub
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $890 to $2,761/night

    Honua Kai Konea 250

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $883 to $4,003/night

    Ho'olei 21-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $874 to $2,906/night

    Island Girl- 30 Gulf Beach Road

    5 Bedrooms3.5 BathroomsSleeps 10
    1 night minstay
    Pool
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $866 to $1,149/night

    Kahana Outrigger #2B1

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $863 to $3,163/night

    Four Blue Palms

    7 BedroomsBathroomsSleeps 30
    2 nights minstay
    Pool
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $863 to $3,637/night

    Nifty Shades of Gray

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $858 to $2,340/night

    Big Island Private Home Alii Drive 6596

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $834 to $2,514/night

    93 Vermillion Way

    6 Bedrooms6.5 BathroomsSleeps 16
    3 nights minstay
    Pool
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $831 to $3,388/night

    Ho'olei 55-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $831 to $4,108/night

    Ho'olei 24-4

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $831 to $2,531/night

    Polo Beach Club 106

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $831 to $3,771/night

    Ho'olei 24-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $831 to $2,294/night

    Big Island Holua Kai 7061

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $830 to $2,947/night

    Maui Dolphin House

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $829 to $3,694/night

    Ho'olei 55-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $828 to $2,071/night

    260 S Wall Street

    4 BedroomsBathroomsSleeps 14
    3 nights minstay
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $828 to $1,864/night

    74 Rolling Dunes Drive

    6 Bedrooms6.5 BathroomsSleeps 14
    3 nights minstay
    Pool
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $821 to $3,805/night

    Highlands Hideaway

    5 BedroomsBathroomsSleeps 14
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $821 to $938/night

    Luxury beachfront home with pool in Islamorada

    3 BedroomsBathroomsSleeps 6
    28 nights minstay
    Pool
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $808 to $3,332/night

    Highlands Slopeside #207

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $808 to $5,132/night

    Snowcloud 203

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $805 to $3,415/night

    River Road Lodge

    7 Bedrooms6.25 BathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub Pets OK
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $791 to $4,300/night

    NEW LISTING!! The Beaver Lodge at Breckenridge

    3 Bedrooms3.5 BathroomsSleeps 10
    2 nights minstay
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $780 to $3,386/night

    Ho'olei 24-6

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $778 to $3,341/night

    Ho'olei 12-4

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $769 to $2,426/night

    Highboy Hideaway | 64 Venice Circle

    6 Bedrooms5.5 BathroomsSleeps 14
    3 nights minstay
    Pool
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $769 to $2,491/night

    High Cotton | 105 Spartina Circle

    6 BedroomsBathroomsSleeps 16
    3 nights minstay
    Pool
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $765 to $3,061/night

    Apres & Fairway Retreat

    5 Bedrooms5.5 BathroomsSleeps 11
    2 nights minstay
    Hot Tub
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $765 to $3,215/night

    New Listing! The Fox Den on French St

    3 BedroomsBathroomsSleeps 12
    2 nights minstay
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $760 to $1,108/night

    Pu'uwai Hale

    4 Bedrooms4.5 BathroomsSleeps 8
    3 nights minstay
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $758 to $4,735/night

    Lionsquare North Tower #402

    5 Bedrooms5.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $758 to $3,918/night

    Sunrise Ski Haus

    4 Bedrooms3.5 BathroomsSleeps 10
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $755 to $10,321/night

    Sorrento Vacation Rental

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub Pets OK
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $754 to $1,416/night

    Kapalua Ridge Villas-#323

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $741 to $5,741/night

    Incredible Executive Private Pet Friendly Home- LR902

    5 Bedrooms4.5 BathroomsSleeps 18
    2 nights minstay
    Hot Tub Pets OK
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $740 to $1,597/night

    Better By The Beach | 164 Red Cedar Way

    4 Bedrooms4.5 BathroomsSleeps 12
    3 nights minstay
    Pool
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $736 to $8,601/night

    Sardinia Vacation Rental

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $735 to $1,506/night

    Hale Lani

    1 Bedroom BathroomSleeps 2
    2 nights minstay
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $734 to $1,575/night

    Memories Await, A Beautiful, Ocean View Villa featuring ...

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $734 to $1,430/night

    Sunset Breeze- Beachfront Pool Home- Monthly Rental

    5 BedroomsBathroomsSleeps 14
    1 night minstay
    Pool Pets OK
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $728 to $1,585/night

    A-S-122KC

    4 Bedrooms3.5 BathroomsSleeps 12
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $727 to $2,751/night

    Wailea Beach Villa J106

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $725 to $1,260/night

    Kona Bubbles

    4 Bedrooms4.5 BathroomsSleeps 8
    3 nights minstay
    Pool
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $714 to $7,974/night

    Abbett Placer Historic Cabin

    7 BedroomsBathroomsSleeps 14
    2 nights minstay
    Hot Tub
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations